[en] Chemical study of the CH₂Cl₂-MeOH (1:1) extract of the sponge Fascaplysinopsis reticulata collected in Mayotte highlighted three new tryptophan derived alkaloids, 6,6'-bis-(debromo)-gelliusine F (1), 6-bromo-8,1'-dihydro-isoplysin A (2) and 5,6-dibromo-8,1'-dihydro-isoplysin A (3), along with the synthetically known 8-oxo-tryptamine (4) and the three known molecules from the same family, tryptamine (5), (E)-6-bromo-2'-demethyl-3'-N-methylaplysinopsin (6) and (Z)-6-bromo-2'-demethyl-3'-N-methylaplysinopsin (7). Their structures were elucidated by 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their antimicrobial and their antiplasmodial activities. Regarding antimicrobial activities, the best compounds are (2) and (3), with minimum inhibitory concentration (MIC) of 0.01 and 1 µg/mL, respectively, towards Vibrio natrigens, and (5), with MIC values of 1 µg/mL towards Vibrio carchariae. In addition the known 8-oxo-tryptamine (4) and the mixture of the (E)-6-bromo-2'-demethyl-3'-N-methylaplysinopsin (6) and (Z)-6-bromo-2'-demethyl-3'-N-methylaplysinopsin (7) showed moderate antiplasmodial activity against Plasmodium falciparum with IC50 values of 8.8 and 8.0 µg/mL, respectively.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Campos, P.-E.; Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de La Réunion, La Réunion, 15 Avenue René Cassin, 97744 Saint-Denis CEDEX 9, France
Pichon, E.; Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de La Réunion, La Réunion, 15 Avenue René Cassin, 97744 Saint-Denis CEDEX 9, France
Moriou, C.; Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay ,av. de la Terrasse, Gif-sur-Yvette, 91198, France
Clerc, P.; Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de La Réunion, La Réunion, 15 Avenue René Cassin, 97744 Saint-Denis CEDEX 9, France
Trépos, R.; Laboratoire des Sciences de l'Environnement MARin (LEMAR), Université de Brest, CNRS, IRD, Ifremer, LEMAR, Plouzane, F-29280, France
Frederich, Michel ; Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
De Voogd, N.; Naturalis Biodiversity Center, Darwinweg 2, CR Leiden, 2333, Netherlands
Hellio, C.; Laboratoire des Sciences de l'Environnement MARin (LEMAR), Université de Brest, CNRS, IRD, Ifremer, LEMAR, Plouzane, F-29280, France
Gauvin-Bialecki, A.; Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments, Faculté des Sciences et Technologies, Université de La Réunion, La Réunion, 15 Avenue René Cassin, 97744 Saint-Denis CEDEX 9, France
Al-Mourabit, A.; Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay ,av. de la Terrasse, Gif-sur-Yvette, 91198, France
Language :
English
Title :
New Antimalarial and Antimicrobial Tryptamine Derivatives from the Marine Sponge Fascaplysinopsis reticulata
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